Naming Amines

Definition of Primary Amines:

Primary amines
are organic chemical compounds that include the functional group -NH2

That is, primary amines are a class or category of organic chemical compounds that include a nitrogen atom connected to two hydrogen atoms by single covalent bonds between the nitogen and each of the hydrogen atoms.

Primary, Secondary and Tertiary Amines:

Above: Simple examples of primary, secondary and tertiary amines

In general amine molecules can vary in size up to very long molecules most of which consist of carbon atoms attached to each other and also to hydrogen atoms. In addition to primary amines, there are other classes of amines such as secondary amines, tertiary amines and cyclic amines. In those cases, although the nitrogen atom (N) is present, the -NH2 group that forms part of primary amines is not complete because in the cases of e.g. secondary and tertiary amines, one or more of the hydrogen atoms is replaced by a carbon bonded to other atoms (e.g. carbons and hydrogens).

The diagram shows that in the case of primary amines, the N is bonded to two Hs and one C whereas in the cases of secondary and tertiary amines the N is bonded to 2 and 3 Cs respectively.

Above: Simple examples of primary, secondary and tertiary amines

In the cases of ...

Primary amides, only one cardon atom is attached to the N. In that case the N is also attached to two Hs.

Secondary amides, two carbon atoms are attached to the N.

Tertiary amides, three carbon atoms are attached to the N.

Amines are named in several ways. The name of the compound is usually formed from either the prefix 'amino-' or the suffix: '-amine.'

The prefix 'N-' indicates which carbon atom the nitrogen atom is attached to.

In the following table of linear primary amines the nitrogen atom is attached to an end carbon, hence it is counted as a 'first' or 'one' carbon atom in all of these examples. Lists of some of the other names also used to refer to these specific simple linear primary amines are included in the table.

Names and Structures of simple Linear Primary Amines

The first 10 members of the homologous series of linear primary amines with the -amine (or '-amino') group attached to the first (= last) carbon atom are:

Carbon atoms in chain

Name

and simple formula

Simple Structure

showing bond types but not accurate bond angles

Other Names = Synonyns*Examples not complete lists

1

methylamine (CH5N)

CH3NH2

methanamine

n-Methylamine

aminomethane

amino methane

2

ethylamine (C2H7N)

CH3CH2NH2

ethanamine

n-Ethylamine

aminoethane

amino ethane

3

propylamine (C3H9N)

CH3CH2CH2NH2

propan-1-amine

n-Propylamine

Propan-1-amine

1-Aminopropane

4

butylamine (C4H11N)

CH3CH2CH2CH2NH2

butan-1-amine

n-Butylamine

amino butane

1-Aminobutane

5

pentylamine (C5H13N)

CH3CH2CH2CH2CH2NH2

pentan-1-amine

n-Pentylamine

Pentanamine

n-Amylamine

1-Aminopentane

6

hexylamine (C6H15N)

CH3CH2CH2CH2CH2CH2NH2

hexan-1-amine

n-Hexylamine

1-Aminohexane

7

heptylamine (C7H17N)

CH3CH2CH2CH2CH2CH2CH2NH2

heptan-1-amine

n-Heptylamine

1-Aminoheptane

8

octylamine (C8H19N)

CH3CH2CH2CH2CH2CH2CH2CH2NH2

octan-1-amine

n-Octylamine

1-Aminooctane

1-Octanamine

Monoctylamine;

9

nonylamine (C9H21N)

CH3CH2CH2CH2CH2CH2CH2CH2CH2NH2

nonan-1-amine

n-Nonylamine

1-Aminononane

10

decylamine (C10H23N)

CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2NH2

decan-1-amine

n-Decylamine

1-Aminodecane

Methylamine (CH5N)

Simple Formula:

CH3NH2

Simple Structure:

*Examples of other / previous names:

methanamine

n-Methylamine

aminomethane

amino methane

Ethylamine (C2H7N)

Simple Formula:

CH3CH2NH2

Simple Structure:

*Examples of other / previous names:

ethanamine

n-Ethylamine

aminoethane

amino ethane

Propylamine (C3H9N)

Simple Formula:

CH3CH2CH2NH2

Simple Structure:

*Examples of other / previous names:

propan-1-amine

n-Propylamine

Propan-1-amine

1-Aminopropane

Butylamine (C4H11N)

Simple Formula:

CH3CH2CH2CH2NH2

Simple Structure:

*Examples of other / previous names:

butan-1-amine

n-Butylamine

amino butane

1-Aminobutane

Pentylamine (C5H13N)

Simple Formula:

CH3CH2CH2CH2CH2NH2

Simple Structure:

*Examples of other / previous names:

pentan-1-amine

n-Pentylamine

Pentanamine

n-Amylamine

1-Aminopentane

Hexylamine (C6H15N)

Simple Formula:

CH3CH2CH2CH2CH2CH2NH2

Simple Structure:

*Examples of other / previous names:

hexan-1-amine

n-Hexylamine

1-Aminohexane

Heptylamine (C7H17N)

Simple Formula:

CH3CH2CH2CH2CH2CH2CH2NH2

Simple Structure:

*Examples of other / previous names:

heptan-1-amine

n-Heptylamine

1-Aminoheptane

Octylamine (C8H19N)

Simple Formula:

CH3CH2CH2CH2CH2CH2CH2CH2NH2

Simple Structure:

*Examples of other / previous names:

octan-1-amine

n-Octylamine

1-Aminooctane

1-Octanamine

Monoctylamine

Nonylamine (C9H21N)

Simple Formula:

CH3CH2CH2CH2CH2CH2CH2CH2CH2NH2

Simple Structure:

*Examples of other / previous names:

nonan-1-amine

n-Nonylamine

1-Aminononane

Decylamine (C10H23N)

Simple Formula:

CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2NH2

Simple Structure:

*Examples of other / previous names:

decan-1-amine

n-Decylamine

1-Aminodecane

According to the International Union of Pure and Applied Chemistry (IUPAC) recommendations for nomenclature of organic chemistry, compounds that include the general structure -C-NH2 may be called amines, see more about naming amines at http://www.acdlabs.com/iupac/nomenclature/79/r79_517.htm.

Why stop at ten carbon atoms (in the chain) ? It doesn't. There are more similar linear amines, or 1-aminoalkanes. We stopped here due to page width.

Important Note: *The synonyms indicated for compounds listed above are just some examples of alternative names found online and believed to have been used to refer to the substance indicated. They have not all been verified and may include common (non-scientific) names and trade names specific to particular suppliers. The purpose of these lists is to give a general indication of the range of names by which these amines are known.

Examples of simple Secondary Amines

Name

and simple formula

Simple Structure

showing bond types but not accurate bond angles

Examples of other names

dimethylamine (CH3)2NH

N-Methylmethanamine

diethylamine (CH3CH2)2NH

N-Ethylethanamine

Dimethylamine (CH3)2NH

Simple Structure:

*Examples of other / previous names:

N-Methylmethanamine

Diethylamine (CH3CH2)2NH

Simple Structure:

*Examples of other / previous names:

N-Ethylethanamine

Other members of this homologous series of secondary amines include dipropylamine, dibutylamine, dipentylamine, dihexylamine and so on.

Examples of simple Tertiary Amines

Name

and simple formula

Simple Structure

showing bond types but not accurate bond angles

Examples of other names

trimethylamine N(CH3)3

N,N-Dimethylmethanamine

triethylamine N(CH2CH3)3

N,N-Diethylethanamine

Trimethylamine N(CH3)3

Simple Structure:

*Examples of other / previous names:

N,N-Dimethylmethanamine

Triethylamine N(CH2CH3)3

Simple Structure:

*Examples of other / previous names:

N,N-Diethylethanamine

Other members of this homologous series of tertiary amines include tripropylamine, tributylamine, tripentylamine, trihexylamine and so on.